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Thioguanine deoxyriboside

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Name

Thioguanine deoxyriboside

EINECS N/A
CAS No. 789-61-7 Density 2.02g/cm3
PSA 154.30000 LogP 0.29300
Solubility N/A Melting Point 190-192 °C
Formula C10H13 N5 O3 S Boiling Point 709.1°C at 760 mmHg
Molecular Weight 283.311 Flash Point 382.6°C
Transport Information N/A Appearance N/A
Safety Questionable carcinogen with experimental carcinogenic data reported. When heated to decomposition it emits toxic vapors of NOx and SOx. Risk Codes N/A
Molecular Structure Molecular Structure of 789-61-7 (6-THIO-2'-DEOXYGUANOSINE) Hazard Symbols Questionable carcinogen.
Synonyms

9H-Purine-6(1H)-thione,2-amino-9-(2-deoxy-b-D-erythro-pentofuranosyl)- (7CI,8CI);2'-Deoxy-6-thioguanosine;2'-Deoxythioguanosine;2'-Desoxy-6-thioguanosine;NSC71261;TGdR;Thioguanine deoxyriboside;b-Thioguanine deoxyriboside;

Article Data 8

Thioguanine deoxyriboside Synthetic route

136112-93-1

Isobutyric acid (2R,3S,5R)-5-(2-isobutyrylamino-6-thioxo-1,6-dihydro-purin-9-yl)-2-isobutyryloxymethyl-tetrahydro-furan-3-yl ester

789-61-7

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine

Conditions
ConditionsYield
With sodium hydroxide In ethanol100%
961-07-9

2'-Deoxyguanosine

789-61-7

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine

Conditions
ConditionsYield
With sodium hydrogensulfide; trifluoroacetic anhydride In pyridine; N,N-dimethyl-formamide65%
With pyridine; sodium hydrogensulfide; trifluoroacetic anhydride 1) 40 min, ice-bath, 2) DMF, 24 h; Yield given. Multistep reaction;
35095-93-3

2-Amino-6-chloro-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)purine

789-61-7

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine

Conditions
ConditionsYield
With hydrogen sulfide; sodium methylate 1) anhydr. MeOH, reflux, 2 h; 2) MeOH, reflux, 1 h; Yield given. Multistep reaction;
4330-21-6

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

789-61-7

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 51 percent / 1) sodium hydride (60percent in oil) / 1) acetonitrile, RT, 30 min; 2) acetonitrile, 20 h
2: 1) H2S/1M sodium methoxide; 2) 1M sodium methoxide / 1) anhydr. MeOH, reflux, 2 h; 2) MeOH, reflux, 1 h
View Scheme
10310-21-1

2-Amino-6-chloropurin

789-61-7

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 51 percent / 1) sodium hydride (60percent in oil) / 1) acetonitrile, RT, 30 min; 2) acetonitrile, 20 h
2: 1) H2S/1M sodium methoxide; 2) 1M sodium methoxide / 1) anhydr. MeOH, reflux, 2 h; 2) MeOH, reflux, 1 h
View Scheme
82921-42-4

2'-deoxy-N2-isobutyrylguanosine 3',5'-diisobutyrate

789-61-7

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1. triethylamine, dimethylaminopyridine, mesitylenesulphonyl chloride, 2a. N-methyl pyrrolidine, 2b. thiolacetic acid / 1. CH2Cl2, RT, 2a. ice bath, 2b. 30 min
2: 100 percent / 2 M NaOH / ethanol
View Scheme
789-61-7

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine

124416-63-3

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine-6-sulfenamide

Conditions
ConditionsYield
With potassium hydroxide; sodium hydroxide; sodium hypochlorite In water 0 deg C to RT;86%
789-61-7

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine

3616-24-8

2-amino-9-(β-D-2'-deoxyribofuranosyl)-purine

Conditions
ConditionsYield
nickel In ethanol; water desulfuration; Heating;77%
With nickel75%
With nickel In water at 50℃; for 13h;73%
789-61-7

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine

121-44-8

triethylamine

2'-deoxy-6-thioguanosine-5'-triphosphate triethylammonium salt

Conditions
ConditionsYield
Stage #1: 2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine With phosphorous acid trimethyl ester; trichlorophosphate at 0℃; for 3h; phosphorylation;
Stage #2: triethylamine With tributyl-amine; bis(tri-n-butylammonium) pyrophosphate In N,N-dimethyl-formamide pH=7.0; phosphorylation;
38%
789-61-7

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine

cobalt(II) nitrate hexahydrate

[Co(2'-deoxy-6-thioguanine)3](NO3)2 dihydrate

Conditions
ConditionsYield
In methanol at 60℃; for 24h;31%

Thioguanine deoxyriboside Chemical Properties

IUPAC Name: 2-Amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purine-6-thione
Molecular Formula: C10H13N5O3S
Molecular Weight: 283.34g/mol
Freely Rotating Bonds: 4
Polar Surface Area: 96.44 Å2
Index of Refraction: 1.93
Molar Refractivity: 66.43 cm3
Molar Volume: 139.5 cm3
Polarizability: 26.33 ×10-24cm3
Surface Tension: 95.1 dyne/cm
Density: 2.02 g/cm3
Flash Point: 382.6 °C
Enthalpy of Vaporization: 108.88 kJ/mol
Boiling Point: 709.1 °C at 760 mmHg
Vapour Pressure: 4.22E-21 mmHg at 25°C
The Cas Register Number of Thioguanine deoxyriboside is 789-61-7 .The chemical synonyms of Thioguanine deoxyriboside (CAS No.789-61-7) are 2’-Deoxy-6-thio-guanosin ; 2’-Deoxythioguanosine ; 2-Amino-9-(2-deoxy-beta-d-erythro-pentofuranosyl)-9h-purine-6(1h)-thion ; Beta-2’-deoxythioguanosine ; Beta-thioguaninedeoxyriboside ; Nci-c01581 ; Tgdr ; 6-Thio-2'-deoxyguanosine .The molecular structure of Thioguanine deoxyriboside (CAS No.789-61-7) is.

Thioguanine deoxyriboside Consensus Reports

NCI Carcinogenesis Bioassay (ipr). clear evidence: rat, NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-TR-57 ,1978. ; NCI Carcinogenesis Bioassay (ipr). inadequate studies:mouse, NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-TR-57 ,1978.

Thioguanine deoxyriboside Safety Profile

Questionable carcinogen with experimental carcinogenic data reported. When heated to decomposition it emits toxic vapors of NOx and SOx.

Thioguanine deoxyriboside Specification

The extinguishing agent of Thioguanine deoxyriboside (CAS No.789-61-7) are dry powder, foam, sand, carbon dioxide, water mist.

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